Trifluoromethylative homo-coupling of carbonyl compounds

Carbonyl compounds are abundant in nature and represent a substantial portion of biomass resources. Despite significant recent progress in homo-coupling of carbonyl compounds, achieving their deoxyfunctionalization homo-coupling remains a highly intricate challenge. Herein, we report an entirely novel reaction paradigm: the trifluoromethylative homo-coupling of carbonyl compounds via hydrazones, which enables the formation of three C(sp3 )-C(sp3 ) bonds in a single step. This method provides a new pathway for synthesizing trifluoromethylative coupling product which has unique applications in both fields of medical and material sciences. Mechanistic investigations have unveiled that the formation of a trifluoromethyl-substituted benzyl radical plays a pivotal role as a key intermediate in this reaction. (c) 2024 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.